Reductive activation of arenes 21.* Reaction of products of two-electron reduction of arenecarbonitriles by alkali metals in liquid ammonia with bromo-and dibromoalkanes

.Production of cyclohexadienyl anions as mentionedabove is accompanied by the formation of an equivalentamount of amide ions. Under the action of amide ions theprimary alkylation products of anions, that is, alkylcyanodihydroarenes undergo dehydrocyanation to givealkylarenes (Scheme 1).The overall yield of alkylation products is 55 to 90%,and the dihydroarene/alkylarene ratio varies in the range0.1—0.5 depending on the nature of the substrate andalkyl halide. For instance, the proportion of dihydroareneincreases both upon replacement of the naphthyl fragment by phenyl one